Syntheses, reactivity, and biological applications of coumarins

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Фев. 19, 2024

This comprehensive review, covering 2021-2023, explores the multifaceted chemical and pharmacological potential of coumarins, emphasizing their significance as versatile natural derivatives in medicinal chemistry. The synthesis functionalization coumarins have advanced with innovative strategies. enabled incorporation diverse functional fragments or construction supplementary cyclic architectures, thereby biological physico-chemical properties compounds obtained were enhanced. unique structure coumarine facilitates binding to various targets through hydrophobic interactions pi-stacking, hydrogen bonding, dipole-dipole interactions. Therefore, this important scaffold exhibits promising applications uncountable fields chemistry (e.g., neurodegenerative diseases, cancer, inflammation).

Язык: Английский

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Electrochemically Enabled C4–H and C3–H Functionalization of 2-Phenyl Quinazoline and Quinoxaline through Dehydrogenative C–H/C–H, C–H/P–H, and C–H/O–H Cross-Coupling

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 6071 - 6095

Опубликована: Апрель 16, 2023

Quinazoline moieties and particularly C4-substituted quinazoline scaffolds are widely distributed in biologically active molecules, thus, direct C4-functionalization of quinazolines is the most convenient way to materialize new, straightforward, sustainable strategies for synthesis useful medicinal targets. Retrospecting that, effort has been directed toward electrocatalytic C4-H bond diversification related electron-deficient N-heterocycles (quinoxaline) offering C4 C3 benzoyl-, acetyl-, phenol-, ether-, phosphonate-, nitroalkane-incorporated via a radical addition pathway under sacrificial oxidant- additive-free conditions. Various coupling partners quinazolines, as well other structurally similar heterocyclic motifs, respond well, providing moderate high yields coupled products along with gram-scale upgradation. Additionally, performed control experiments cyclic voltammetry investigations also nicely justified proposed mechanism process. Further, late-stage functionalization leading indolo quinolines vinyl-sulfonated using ruthenium-catalyzed skeletal transformation benzoylated 3b appropriated developed methodology. Finally, this reaction can be summarized (a) anodic activation functionalized Hantzsch ester furnish key species; (b) an activated N-heterocycle; (c) oxidation target product without assistance any metal chelation.

Язык: Английский

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Ru(ii) catalyzed chelation assisted C(sp²)–H bond functionalization along with concomitant (4 + 2) annulation

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(27), С. 5567 - 5586

Опубликована: Янв. 1, 2023

Efficacious protocols have been established to synthesize a structurally privileged Π-extended coumarin-fused pyridone nucleus by activating the vinylic C(sp2)-H bond of coumarin-3-carboxamide under influence inexpensive Ru(II)-metal. Here an N-methoxy carboxamide entity has exploited as chelating fragment manifest functionalization with concomitant (4 + 2) annulation reaction, resulting in heterocyclic ring-forming along sulfoxonium ylide and iodonium representative bench-stable carbene surrogates. This diverse heterocycle formation via insertion strategies, is further expanded activate ortho-C(sp2)-H bonds different heterocycles employing sp2-N moiety directing group develop acyl-alkylated/alkenylated quinazolines, isoxazoles highly fluorescent pyridone-N-oxides. Intriguingly, during evaluation versatility current protocols, one-pot double C-H activation rationalized presence ylide, which results biologically potent benzimidazole-fused coumarin-centered bridge-headed polycyclic heteroarenes. Furthermore, chemo-selective late-stage synthetic transformation being designed differently substituted analogues switching nature reducing agent. In addition, photophysical experiment was done on one pyridine-N-oxide compound (7e) delightfully it exhibited fluorescence quenching activity selectively Al3+ ions, appears be unique feature our methodology. Finally, upon correlation merit developed pathways, mediated strategy superior.

Язык: Английский

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Regioselective [3+2]‐Spiroannulation and [4+n]‐Annulation Approaches through Activation of C−H Bond Facilitated by Ru(II) as Catalyst: Role of Solvent Selectivity

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1863 - 1876

Опубликована: Фев. 21, 2024

Abstract Ru(II)‐catalyzed and solvent‐switched [3+2]‐spiroannulation [4+n] (n=1, 2, 3) annulations of 2‐aryl quinazolinone or 2‐aryl‐2,3‐dihydrophthalazine‐1,4‐diones with ynones alkynyl alcohol 1,3‐diynes under mild reaction conditions have been analyzed. These reactions take place in the presence appropriate solvent features a redox‐neutral pathway. Ynone serves as an ‘atypical one‐carbon unit’ [4+1] annulation generates tetrasubstituted carbon center bearing diverse heterocycles through [3+2] strategies. Post transformations synthesized spiro‐products augments potential developed methodology.

Язык: Английский

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Coumarin-Fused Nitrogenous Heterocycles: An Exploration of Annulation Strategies

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Март 21, 2025

Abstract Driven by advances in the pharmaceutical industry and materials science, search for innovative strategies synthesis functionalization of coumarin-fused nitrogenous heterocycles has intensified. These compounds, which combine bioactive coumarin core with various nitrogen-containing heterocycles, are significant interest due to their diverse biological activities promising potential applications. Traditional methods synthesizing these hybrid structures often encounter challenges such as low yields, limited functional group compatibility rigorous reaction conditions. To address challenges, there is a growing need development advanced synthetic that can effectively efficaciously produce aforementioned heterocyclic scaffolds. Towards this goal, annulation (e.g., cyclization, condensation, multicomponent reactions, transition-metal-catalyzed etc.) represent pivotal techniques construct evade constraints conventional approaches. In account, we highlight our recent progress on construction complex scaffolds order pave way further developments dynamic field. 1 Introduction 2 Exploring Acid-Catalyzed Annulation Strategies 3 Based C–H Activation 4 Oxidative 5 Conclusion

Язык: Английский

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Fused Furan Moieties from Enol-like Compounds and β-Keto Sulfoxonium Ylides Involving sp² C–H Activation and Concomitant Tandem C–O Annulation

Organic Letters, Год журнала: 2023, Номер 25(24), С. 4493 - 4497

Опубликована: Июнь 9, 2023

An efficient and fascinating protocol has been devised for the preparation of fused furan moieties involving a Rh(II) catalyzed one-pot C–H activation/concomitant tandem annulation process, employing an enolic compound β-keto sulfoxonium ylide as reacting conjugates. The developed technique demands only Rh2(TFA)4 catalyst to proceed forward is devoid additional metallic or nonmetallic additives. skeletal transformation naphthoquinone highly decorated indolizines promising synthetic application.

Язык: Английский

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Recent advances in the synthesis of chromenone fused pyrrolo[2,1-a]isoquinoline derivatives

New Journal of Chemistry, Год журнала: 2023, Номер 47(48), С. 22246 - 22268

Опубликована: Янв. 1, 2023

This review, from 2016 to 2022, summarizes advances in the synthesis of 2- and 4-chromenones fused five-membered ring pyrrolo[2,1- a ]isoquinolines diverse orientations highlighting modes construction by classical transition metal-catalyzed methods.

Язык: Английский

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Cascade [4 + 1] Annulation through Activation of the C(sp²)–H Bond Enabling Benzothiadiazinoisoindolcarboxylate, Benzothiadiazinoisoindole, and Benzothiadiazinoisoindolepyrrolidinedione as Hybrid Spiro-Heterocyclic Frameworks

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7705 - 7717

Опубликована: Май 17, 2024

Two structurally distinct and biologically privileged succinimide isoindole heteroarenes bearing benzothiadiazinedioxide motif-centered hybrid conjugates are proficiently achieved through Rh(III)-catalyzed sequential C(sp

Язык: Английский

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Harnessing the benzyne insertion consequence to enable π-extended pyrido-acridine and quinazolino-phenanthridine

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(27), С. 5591 - 5602

Опубликована: Янв. 1, 2024

Protocols have been devised for π-extended pyrido-acridines and quinazolino-phenanthridines, applying Rh( iii )- Pd( ii )-mediated catalytic courses. The parent compounds are realized from 2-aminobenzonitrile apposite benzyne precursor respectively.

Язык: Английский

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An Overview of the Synthesis of 3,4-Fused Pyrrolocoumarins of Biological Interest

Molecules, Год журнала: 2024, Номер 29(12), С. 2748 - 2748

Опубликована: Июнь 9, 2024

3,4-Fused pyrrolocoumarins, synthetically prepared or naturally occurring, possess interesting biological properties. In this review, the synthetic strategies for synthesis of title compounds are presented along with their activities. Two routes followed that synthesis. one, pyrrole ring is formed from coumarin derivatives, such as aminocoumarins other coumarins. approach, pyranone moiety built an existing derivative through simultaneous formation and frameworks. The above syntheses achieved via 1,3-dipolar cycloaddition reactions, Michael reaction, aza-Claisen rearrangement multi-component reactions (MCR), well metal-catalyzed reactions. Pyrrolocoumarins present cytotoxic, antifungal, antibacterial, α-glucosidase inhibition, antioxidant, lipoxygenase (LOX) fluorescent activities, benzodiazepine receptor ability.

Язык: Английский

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